Sodium Hydroxide → 2,2'-{Propane-2,2-diylbis[(4,1-phenylene)oxy]}diacetic acid

HRID 1166432Notes

Reaction equation

HRID 1166432 reaction equation
C([O:3][C:4]([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:17]2[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=2)([CH3:16])[CH3:15])=[CH:10][CH:9]=1)=[O:5])C.[OH-].[Na+]>CO>[C:23]([CH2:22][O:21][C:20]1[CH:19]=[CH:18][C:17]([C:14]([C:11]2[CH:10]=[CH:9][C:8]([O:7][CH2:6][C:4]([OH:5])=[O:3])=[CH:13][CH:12]=2)([CH3:16])[CH3:15])=[CH:29][CH:28]=1)([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12359780HCID 12359780, compound

Product 1

HCID 123597752,2'-{Propane-2,2-diylbis[(4,1-phenylene)oxy]}diacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.7 g of ethyl 4-[1-(4-ethoxycarbonylmethoxyphenyl)-1-methylethyl]phenoxyacetate are dissolved in 20 ml of methanol, and 16.7 g of 10% strength sodium hydroxide solution are added. The mixture is heated to boiling under reflux for 3 hours, after which it is cooled down and the methanol is then distilled off on a rotary evaporator. The residue is diluted with water and acidified to pH 2 with 2 N HCl; the colorless precipitate is then filtered off with suction, washed with water and dried in vacuo over calcium chloride. 5.5 g of the title compound, having a m.p. of 177-179° C., are obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. temperatureafter which it is cooled down
  4. distillationthe methanol is then distilled off on a rotary evaporator
  5. additionThe residue is diluted with water
  6. filtrationthe colorless precipitate is then filtered off with suction
  7. washwashed with water
  8. dry with materialdried in vacuo over calcium chloride
  9. customare obtained

Sources & evidence

ORD record
ord-29302ede671d47df8206d0d0cd382dff
Source dataset
uspto-grants-2003_09
Patent number
US06613769B1

Reaction notes

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